Ethanol → Ethyl 5-aminopyridine-2-carboxylate

HRID 85161Notes

Reaction equation

HRID 85161 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.O=S(Cl)Cl.[CH2:15](O)[CH3:16]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:15][CH3:16])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 41797265-Aminopyridine-2-carboxylic acid

Product 1

HCID 13816714Ethyl 5-aminopyridine-2-carboxylateYield 75%

Procedure

To a solution of 5-aminopicolinic acid (110; 8.4 g, 60.8 mmol) in ethanol (100 mL) was added SOCl2 (14.5 g, 120 mmol) at 0° C. The mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust pH=9. The resulting mixture was filtered and the solids were dried under reduced pressure to afford ethyl 5-aminopicolinate 111 (7.5 g, 75%).

Workup

  1. temperatureunder reflux for 12 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionEnough saturated aqueous Na2CO3 solution was added
  4. filtrationThe resulting mixture was filtered
  5. customthe solids were dried under reduced pressure

Sources & evidence

ORD record
ord-7283f9127a334f25883651b5e67ea286
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

Loading…